benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

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Chemical Name:benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester
CAS No.:866021-72-9
Molecular Formula:C₂₃H₃₂O₇
Molecular Weight:420.503
Hs Code.:

Synonyms:benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

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Chemical Property of benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

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Technology Process of benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

There total 5 articles about benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

: 866021-71-8
(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 160666-92-2
(S)-2-benzoyloxypentan-3-one

: benzoic acid 4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

: 866021-72-9
benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

Guidance literature:: (S)-2-benzoyloxypentan-3-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at 0 ℃;

(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde; at -78 ℃;

With dihydrogen peroxide;
DOI:10.1021/ol051405x

Reference yield:

: 866022-02-8
(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 866021-72-9
benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran

2.1: TBAF / tetrahydrofuran / 0 °C

3.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

4.1: c-Hex₂BCl; Et₃N / diethyl ether / 0 °C

4.2: -78 °C

4.3: 79 percent / aq. H₂O₂

With dicyclohexylboron chloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3.1: Dess-Martin oxidation;
DOI:10.1021/ol051405x

Reference yield:

: 866022-05-1
tert-butyl-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethoxy]dimethylsilane

: 866021-72-9
benzoic acid (1S,3R,4S)-4-hydroxy-4-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethyl-2-oxobutyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: TBAF / tetrahydrofuran / 0 °C

2.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

3.1: c-Hex₂BCl; Et₃N / diethyl ether / 0 °C

3.2: -78 °C

3.3: 79 percent / aq. H₂O₂

With dicyclohexylboron chloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1021/ol051405x